Portland Cottage Rentals

KAYAK searches hundreds of travel sites at once for cottage deals in Portland

Here is why travelers choose KAYAK

Free to useThere are no hidden charges or fees.

Filter your dealsFilter by free cancellation, free breakfast and more.

Millions of reviewsCheck ratings based on millions of real guest reviews.

Recommended by KAYAK
Useful Info
Recommended by KAYAK

Best Portland cottage rentals

Go to map

Search by review score

6+ Okay7+ Good8+ Great9+ Excellent

Search by price

$180 - $413$413 - $645$645 - $877$877 - $1,109$1,109+ per night

Search by freebies

Free breakfastFree parkingFree cancellationFree internetFree airport shuttle

Most recommended cottage rentals in Portland

Show all
Classic Island Cottage - Peaks Island - Balcony
Classic Island Cottage
Peaks Island, ME
9.9Wonderful(41)
Cottage
$405+
Check availability
Classic Turn of the Century Island Summer Cottage - Peaks Island - Bedroom
Classic Turn of the Century Island Summer Cottage
Peaks Island, ME
10Wonderful(3)
Cottage
$723+
Check availability
Enjoy Sweeping Waterfront View, Watch Lobster Boats from Porch - Portland - Beach
Enjoy Sweeping Waterfront View, Watch Lobster Boats from Porch
Portland, ME
9.6Wonderful(10)
Cottage
$626+
Check availability
Charming Peaks Island Cottage - Peaks Island - Kitchen
Charming Peaks Island Cottage
Peaks Island, ME
9.4Wonderful(61)
Cottage
$249+
Check availability
Peaks Island Maine Seaside Cottage: hot tub/roof decks/4 season - Portland - Living room
Peaks Island Maine Seaside Cottage: hot tub/roof decks/4 season
Portland, ME
9.4Wonderful(22)
Cottage
$653+
Check availability
Oceanview, Handicap Friendly, Dogs & Babies Welcome. Watch the Seashore parade! - Peaks Island - Kitchen
Oceanview, Handicap Friendly, Dogs & Babies Welcome. Watch the Seashore parade!
Peaks Island, ME
9.8Wonderful(15)
Cottage
$546+
Check availability
Hollywood meets seaside charm in the former cottage of famed director, John Ford - Peaks Island - Bedroom
Hollywood meets seaside charm in the former cottage of famed director, John Ford
Peaks Island, ME
9.8Wonderful(33)
Cottage
$526+
Check availability
Classic Family Cottage, Ocean View From Porch, Peaceful Rural Location - Portland - Living room
Classic Family Cottage, Ocean View From Porch, Peaceful Rural Location
Portland, ME
10Wonderful(13)
Cottage
$872+
Check availability
The Beach House Cottage is on a Sandy Beach! Amazing Views!! - Peaks Island - Kitchen
The Beach House Cottage is on a Sandy Beach! Amazing Views!!
Peaks Island, ME
9.7Wonderful(15)
Cottage
$1,199+
Check availability
3BR Cottage Parking A Peaceful Oasis on Munjoy Hill - Portland - Kitchen
3BR Cottage Parking A Peaceful Oasis on Munjoy Hill
Portland, ME
10Wonderful(2)
Cottage
$413+
Check availability
Relaxing Retreat! 6 Miles from the beach and close to Portland! - Scarborough - Living room
Relaxing Retreat! 6 Miles from the beach and close to Portland!
Scarborough, ME
10Wonderful(4)
Cottage
$247+
Check availability
Sun-lit, 2 Bedroom Guest cottage on 27 Acres in Freeport - Freeport - Living room
Sun-lit, 2 Bedroom Guest cottage on 27 Acres in Freeport
Freeport, ME
Cottage
$353+
Check availability
Updated Historical beach cottage in Scarborough near beaches, old orchard & more - Scarborough - Patio
Updated Historical beach cottage in Scarborough near beaches, old orchard & more
Scarborough, ME
10Wonderful(3)
Cottage
$312+
Check availability
Charming Pine Point Cottage - 2 Blocks To Ocean! - Scarborough
Charming Pine Point Cottage - 2 Blocks To Ocean!
Scarborough, ME
9.6Wonderful(17)
Cottage
$543+
Check availability
506 Preble St Duplex 2 Bedrooms 1.5 Bathroom Duplex - South Portland
506 Preble St Duplex 2 Bedrooms 1.5 Bathroom Duplex
South Portland, ME
Cottage
$299+
Check availability
'Heron Cottage' on Casco Bay w/ Deck & Boat Dock! - Freeport
'Heron Cottage' on Casco Bay w/ Deck & Boat Dock!
Freeport, ME
8.0Very good(1)
Cottage
$468+
Check availability
Useful Info

Good to know

Low season

High season

Average price (weeknight)

Average price (weekend night)

September
July
$333
$389
Cheapest month to stay with an average 45% drop in price.
Most expensive month to stay with an average 172% rise in price.
Average Sun - Thu price over the last 2 weeks.
Average Fri & Sat price over the last 2 weeks.

KAYAK's top tips for finding Portland vacation rental deals

  • For the cheapest cottage rental in Portland, try to visit during the low season and outside of main travel peaks. The cheapest rates can be found in September and November.
  • The cheapest night of the week to rent a cottage in Portland is Wednesday. On the other hand, the most expensive is Saturday.

FAQs when Booking a cottage in Portland

  • How much is a cottage rental for a week in Portland?

    The average price for a weekly Portland cottage rental found by KAYAK users in the last 2 weeks is $2,580 ($369/night). Though this can obviously vary depending on the time of year of your stay and when you make the booking.

  • How much is a cottage rental for a month in Portland?

    The average price for a monthly Portland cottage rental found by KAYAK users in the last 2 weeks is $8,843 ($295/night).

Where to stay in Portland?

Our map will help you find the perfect place to stay in Portland by showing you the exact location of each vacation rental.

Everything you need to know for your stay in Portland